ES2377661T3 - Nuevos compuestos III - Google Patents
Nuevos compuestos III Download PDFInfo
- Publication number
- ES2377661T3 ES2377661T3 ES06835882T ES06835882T ES2377661T3 ES 2377661 T3 ES2377661 T3 ES 2377661T3 ES 06835882 T ES06835882 T ES 06835882T ES 06835882 T ES06835882 T ES 06835882T ES 2377661 T3 ES2377661 T3 ES 2377661T3
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- acetamide
- benzimidazol
- nitro
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 142
- -1 phenyloxymethyl Chemical group 0.000 claims abstract description 325
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 156
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 46
- 125000001424 substituent group Chemical group 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 238000011282 treatment Methods 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 208000002193 Pain Diseases 0.000 claims description 27
- 208000035475 disorder Diseases 0.000 claims description 24
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
- 230000001154 acute effect Effects 0.000 claims description 21
- 230000001684 chronic effect Effects 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
- 230000036407 pain Effects 0.000 claims description 15
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 10
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 9
- 206010065390 Inflammatory pain Diseases 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 208000004296 neuralgia Diseases 0.000 claims description 8
- 208000021722 neuropathic pain Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- 208000024891 symptom Diseases 0.000 claims description 7
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 208000005298 acute pain Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 208000005615 Interstitial Cystitis Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 208000008035 Back Pain Diseases 0.000 claims description 4
- 206010011224 Cough Diseases 0.000 claims description 4
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
- 208000001640 Fibromyalgia Diseases 0.000 claims description 4
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 4
- 208000008930 Low Back Pain Diseases 0.000 claims description 4
- 208000001294 Nociceptive Pain Diseases 0.000 claims description 4
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 4
- 206010033645 Pancreatitis Diseases 0.000 claims description 4
- 208000000450 Pelvic Pain Diseases 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 206010047700 Vomiting Diseases 0.000 claims description 4
- VRAKDAYLTPMBAW-UHFFFAOYSA-N [O-][N+](=O)ClC#N Chemical group [O-][N+](=O)ClC#N VRAKDAYLTPMBAW-UHFFFAOYSA-N 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 201000003146 cystitis Diseases 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 208000020629 overactive bladder Diseases 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 208000009935 visceral pain Diseases 0.000 claims description 4
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- UKEQWYSCLIWAHQ-UHFFFAOYSA-N 2-(7-chlorobenzimidazol-1-yl)-n-[1-(6-propan-2-yloxypyridin-3-yl)ethyl]acetamide Chemical compound C1=NC(OC(C)C)=CC=C1C(C)NC(=O)CN1C2=C(Cl)C=CC=C2N=C1 UKEQWYSCLIWAHQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- YBWAPUVFZKXKIE-UHFFFAOYSA-N n-[1-(6-tert-butyl-4-methylpyridin-3-yl)ethyl]-2-(7-cyanobenzimidazol-1-yl)acetamide Chemical compound C1=NC2=CC=CC(C#N)=C2N1CC(=O)NC(C)C1=CN=C(C(C)(C)C)C=C1C YBWAPUVFZKXKIE-UHFFFAOYSA-N 0.000 claims description 2
- CFERFOIUABURIX-UHFFFAOYSA-N n-[1-(6-tert-butylpyridin-3-yl)ethyl]-2-(7-cyanobenzimidazol-1-yl)acetamide Chemical compound C1=NC2=CC=CC(C#N)=C2N1CC(=O)NC(C)C1=CC=C(C(C)(C)C)N=C1 CFERFOIUABURIX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 206010011796 Cystitis interstitial Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 238000000034 method Methods 0.000 description 47
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- 108010025083 TRPV1 receptor Proteins 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000013067 intermediate product Substances 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 229960002504 capsaicin Drugs 0.000 description 13
- 235000017663 capsaicin Nutrition 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- DBVQWDRJFZMDDL-UHFFFAOYSA-N 1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethanamine Chemical compound CC(N)C1=CC=C(OCC(F)(F)F)N=C1 DBVQWDRJFZMDDL-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
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- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 7
- JRYYVMDEUJQWRO-UHFFFAOYSA-N 2-methylnicotinamide Chemical compound CC1=NC=CC=C1C(N)=O JRYYVMDEUJQWRO-UHFFFAOYSA-N 0.000 description 6
- JHHURKBLEGFPPB-UHFFFAOYSA-N 6-tert-butylpyridine-3-carbonitrile Chemical compound CC(C)(C)C1=CC=C(C#N)C=N1 JHHURKBLEGFPPB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 6
- CTMUOPMCEIJFPH-UHFFFAOYSA-N 2-(7-cyanobenzimidazol-1-yl)acetic acid Chemical compound C1=CC(C#N)=C2N(CC(=O)O)C=NC2=C1 CTMUOPMCEIJFPH-UHFFFAOYSA-N 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- HRQVDFYSVVIRIK-UHFFFAOYSA-N N-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound CC(=O)Nn1cnc2cccc([N+]([O-])=O)c12 HRQVDFYSVVIRIK-UHFFFAOYSA-N 0.000 description 5
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- 239000003039 volatile agent Substances 0.000 description 5
- XWOYHZILMRKZMH-UHFFFAOYSA-N 1-(6-tert-butylpyridin-3-yl)ethanamine Chemical compound CC(N)C1=CC=C(C(C)(C)C)N=C1 XWOYHZILMRKZMH-UHFFFAOYSA-N 0.000 description 4
- KEDZLCLUXLHIKQ-UHFFFAOYSA-N 1-[6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl]ethanamine Chemical compound CC(N)C1=CC=C(OCC(F)(F)C(F)F)N=C1 KEDZLCLUXLHIKQ-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- JPEGBZFDDUESBF-UHFFFAOYSA-N 1-(6-cyclopentyloxypyridin-3-yl)ethanamine Chemical compound N1=CC(C(N)C)=CC=C1OC1CCCC1 JPEGBZFDDUESBF-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
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Landscapes
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| PCT/SE2006/001467 WO2007073303A2 (en) | 2005-12-23 | 2006-12-21 | Novel benzimidazole derivatives as vanilloid receptor 1 (vrl) inhibitors |
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| SE0301446D0 (sv) | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | New Compounds |
| UY30048A1 (es) * | 2005-12-23 | 2007-07-31 | Astrazeneca Ab | Derivados sustituidos de la n,2-(1h-benzimidazol-1-il) acetamida, composiciones farmacéuticas conteniéndolos, procesos de preparación y aplicaciones |
| TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
| WO2009054983A1 (en) * | 2007-10-24 | 2009-04-30 | Merck & Co., Inc. | Heterocycle amide t-type calcium channel antagonists |
| NZ587771A (en) | 2008-04-18 | 2011-05-27 | Dae Woong Pharma | Novel benzoxazine benzimidazole derivatives, pharmaceutical composition comprising same, and a use thereof |
| DE112011102008B4 (de) | 2010-06-15 | 2022-04-21 | Merck Patent Gmbh | Metallkomplexe |
| KR101293384B1 (ko) | 2010-10-13 | 2013-08-05 | 주식회사 대웅제약 | 신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도 |
| WO2016055582A1 (en) * | 2014-10-08 | 2016-04-14 | Thomas Helledays Stiftelse För Medicinsk Forskning | Heterocyclic compounds as dctpp1 modulators |
| JO3719B1 (ar) | 2014-11-20 | 2021-01-31 | Takeda Pharmaceuticals Co | 4- أوكسو-4،3- داي هيدرو-3،2،1- بنزوترايازينات كمواد ضابطة لأجل gpr139 |
| JP2018052817A (ja) * | 2015-01-21 | 2018-04-05 | 大日本住友製薬株式会社 | 新規ベンズイミダゾール誘導体およびその医薬用途 |
| US11186564B2 (en) | 2016-08-04 | 2021-11-30 | Sunovion Pharmaceuticals Inc. | Dual NAV1.2/5HT2a inhibitors for treating CNS disorders |
| EP3908574A4 (en) * | 2019-01-08 | 2022-10-26 | Neomed Institute | CRYSTALLINE FORMS OF (S)-2-(7-CYANO-1H-BENZIMIDAZOL-1YL)-N-{1-[4-(1-CYANO-1-METHYLETHYL)PHENYL]ETHYL}ACETAMIDE |
| CR20220160A (es) | 2019-09-16 | 2022-06-16 | Takeda Pharmaceuticals Co | Derivados de piridazin-3(2h)-ona fusionados con azol |
| CA3218090A1 (en) | 2021-05-10 | 2022-11-17 | Magnus HALLDIN | New formulations and uses |
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| GB1186504A (en) | 1966-10-15 | 1970-04-02 | Fisons Pest Control Ltd | Substituted Heterocyclic Compounds |
| IT1036004B (it) * | 1968-05-21 | 1979-10-30 | Abc Ist Biolog Chem Spa | Acidt 3 indolil adetoidrossamici |
| BE793718A (fr) | 1972-01-07 | 1973-07-05 | Merck & Co Inc | Aminobenzimidazoles |
| US4136189A (en) * | 1975-09-16 | 1979-01-23 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 2-(5-nitro-furfurylidene)-amino-benzimidoles and fungicidal compositions containing the same |
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-
2006
- 2006-12-20 UY UY30048A patent/UY30048A1/es unknown
- 2006-12-20 AR ARP060105673A patent/AR058705A1/es not_active Application Discontinuation
- 2006-12-20 TW TW095148018A patent/TW200736227A/zh unknown
- 2006-12-21 EP EP06835882A patent/EP1966156B1/en active Active
- 2006-12-21 CN CN2006800533688A patent/CN101389610B/zh not_active Expired - Fee Related
- 2006-12-21 JP JP2008547169A patent/JP2009521431A/ja active Pending
- 2006-12-21 US US11/614,346 patent/US7618993B2/en active Active
- 2006-12-21 WO PCT/SE2006/001467 patent/WO2007073303A2/en not_active Ceased
- 2006-12-21 RU RU2008122404/04A patent/RU2427573C2/ru not_active IP Right Cessation
- 2006-12-21 ES ES06835882T patent/ES2377661T3/es active Active
- 2006-12-21 AT AT06835882T patent/ATE538101T1/de active
- 2006-12-21 UA UAA200807385A patent/UA96277C2/ru unknown
- 2006-12-21 KR KR1020087017908A patent/KR20080080212A/ko not_active Abandoned
- 2006-12-21 BR BRPI0620410-4A patent/BRPI0620410A2/pt not_active IP Right Cessation
- 2006-12-21 AU AU2006327320A patent/AU2006327320B2/en not_active Ceased
- 2006-12-21 NZ NZ569923A patent/NZ569923A/en unknown
- 2006-12-21 CA CA002634804A patent/CA2634804A1/en not_active Abandoned
-
2008
- 2008-05-27 IL IL191753A patent/IL191753A0/en unknown
- 2008-06-12 ZA ZA200805162A patent/ZA200805162B/xx unknown
- 2008-06-27 EC EC2008008584A patent/ECSP088584A/es unknown
- 2008-07-22 NO NO20083246A patent/NO20083246L/no not_active Application Discontinuation
-
2009
- 2009-10-14 US US12/578,730 patent/US8168668B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101389610A (zh) | 2009-03-18 |
| EP1966156B1 (en) | 2011-12-21 |
| ECSP088584A (es) | 2008-07-30 |
| IL191753A0 (en) | 2008-12-29 |
| WO2007073303A3 (en) | 2007-08-30 |
| UY30048A1 (es) | 2007-07-31 |
| US7618993B2 (en) | 2009-11-17 |
| WO2007073303A2 (en) | 2007-06-28 |
| CA2634804A1 (en) | 2007-06-28 |
| RU2427573C2 (ru) | 2011-08-27 |
| BRPI0620410A2 (pt) | 2011-11-08 |
| NZ569923A (en) | 2011-04-29 |
| KR20080080212A (ko) | 2008-09-02 |
| RU2008122404A (ru) | 2010-01-27 |
| AU2006327320B2 (en) | 2009-12-10 |
| US20080171770A1 (en) | 2008-07-17 |
| CN101389610B (zh) | 2011-12-07 |
| JP2009521431A (ja) | 2009-06-04 |
| NO20083246L (no) | 2008-09-11 |
| ATE538101T1 (de) | 2012-01-15 |
| US8168668B2 (en) | 2012-05-01 |
| AU2006327320A1 (en) | 2007-06-28 |
| AR058705A1 (es) | 2008-02-20 |
| US20100286202A1 (en) | 2010-11-11 |
| HK1121755A1 (en) | 2009-04-30 |
| UA96277C2 (en) | 2011-10-25 |
| TW200736227A (en) | 2007-10-01 |
| ZA200805162B (en) | 2009-11-25 |
| EP1966156A2 (en) | 2008-09-10 |
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